US4076809A
Expired / Lapsed
US
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Phosphonoureide and phosphonothioureide anthelmintics
Assignee: GlaxoSmithKline LLC
•
Filing: 1975-10-28
•
Granted: 1978-02-28
•
Expires: 1995-10-28
Abstract
Abstract This invention relates to novel anthelmintic compounds containing an arylene or divalent heterocyclic ring whose free valences are satisfied by 1. a disubstituted phosphoryl ureido or thioureido group and 2. an amino group or a substituted amido or thioamido group, To compositions containing them, and to methods of using them for the treatment of intestinal parasites in mammals and birds.
Inventors
- 👤 W. David Weir
- 👤 Edward E. Kilbourn
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 04:36
CPC Classifications
C; C07; C07F; C07F9/00; C07F9/02; C07F9/06; C07F9/22; C07F9/24; C07F9/2454; C07F9/2479; C07F9/2487
Claims Analysis
Total Claims: 59
Claim 1
Independent Claim
7 words
A compound of the formula: ##STR106## wherein
Claim 2
Dependent Claim
7 words
A compound of the formula: ##STR106## wherein
Claim 3
Dependent Claim
42 words
A is a divalent arylene group optionally substituted with a. halogen; b. cyano; c. nitro; d. di(C 1 -C 18 ) alkylamino; e. vicinal alkylene of from 2 to 6 carbon atoms; or f. a group of the formula: R.sup.1 (A').sub.a wherein
Claim 4
Dependent Claim
42 words
A is a divalent arylene group optionally substituted with a. halogen; b. cyano; c. nitro; d. di(C 1 -C 18 ) alkylamino; e. vicinal alkylene of from 2 to 6 carbon atoms; or f. a group of the formula: R.sup.1 (A').sub.a wherein
Claim 5
Dependent Claim
3 words
R 1 is
Claim 6
Dependent Claim
3 words
R 1 is
Claim 7
Dependent Claim
210 words
an alkyl group of from 1 to 4 carbon atoms; 2. a substituted or unsubstituted aromatic group containing from 6 to 10 carbon atoms in the aromatic ring; A' is oxygen, sulfur, sulfinyl, sulfonyl or carbonyl; and a is an integer of 0 to 1; R is a. hydrogen; b. (C 1 -C 10 ) alkyl; c. (C 1 -C 10 ) haloalkyl; d. (C 3 -C 6 ) cycloalkyl; e. (C 2 -C 11 ) alkoxyalkyl; f. (C 1 -C 10 ) cyanoalkyl; g. (C 3 -C 6 ) alkenyl; h. (C 3 -C 6 ) haloalkenyl; i. (C 3 -C 6 ) alkynyl; j. (C 3 -C 6 ) haloalkynyl; k. optionally substituted aralkyl of up to 11 carbon atoms; l. substituted or unsubstituted (C 6 -C 10 ) aryl; Y is R', OR', N(R') 2 or SR' and Y' is OR', N(R') 2 or SR' wherein R' is alkyl (C 1 -C 4 ), substituted alkyl (C 1 -C 4 ), aralkyl (C 7 -C 10 ), alkenyl (C 1 -C 4 ), substituted alkenyl (C 1 -C 4 ), phenyl, substituted phenyl, naphthyl or substituted naphthyl X is oxygen or sulfur; X' is oxygen or sulfur; and Z is a group of the formula: ##STR107## wherein
Claim 8
Dependent Claim
210 words
an alkyl group of from 1 to 4 carbon atoms; 2. a substituted or unsubstituted aromatic group containing from 6 to 10 carbon atoms in the aromatic ring; A' is oxygen, sulfur, sulfinyl, sulfonyl or carbonyl; and a is an integer of 0 to 1; R is a. hydrogen; b. (C 1 -C 10 ) alkyl; c. (C 1 -C 10 ) haloalkyl; d. (C 3 -C 6 ) cycloalkyl; e. (C 2 -C 11 ) alkoxyalkyl; f. (C 1 -C 10 ) cyanoalkyl; g. (C 3 -C 6 ) alkenyl; h. (C 3 -C 6 ) haloalkenyl; i. (C 3 -C 6 ) alkynyl; j. (C 3 -C 6 ) haloalkynyl; k. optionally substituted aralkyl of up to 11 carbon atoms; l. substituted or unsubstituted (C 6 -C 10 ) aryl; Y is R', OR', N(R') 2 or SR' and Y' is OR', N(R') 2 or SR' wherein R' is alkyl (C 1 -C 4 ), substituted alkyl (C 1 -C 4 ), aralkyl (C 7 -C 10 ), alkenyl (C 1 -C 4 ), substituted alkenyl (C 1 -C 4 ), phenyl, substituted phenyl, naphthyl or substituted naphthyl X is oxygen or sulfur; X' is oxygen or sulfur; and Z is a group of the formula: ##STR107## wherein
Claim 9
Dependent Claim
55 words
R and R 1 are as defined above; n is an integer of 0 to 1; B is carbonyl, sulfinyl, or sulfonyl; Q is alkylene of from 2 to 4 carbon atoms; and X" is oxygen or sulfur, provided that when X" is sulfur, X is oxygen; or a pharmacuetically acceptable salt of said compound.
Claim 10
Dependent Claim
55 words
R and R 1 are as defined above; n is an integer of 0 to 1; B is carbonyl, sulfinyl, or sulfonyl; Q is alkylene of from 2 to 4 carbon atoms; and X" is oxygen or sulfur, provided that when X" is sulfur, X is oxygen; or a pharmacuetically acceptable salt of said compound.
Claim 11
Dependent Claim
10 words
A compound according to claim 1, having the formula: ##STR108##
Claim 12
Dependent Claim
1 words
wherein
Claim 13
Dependent Claim
1 words
wherein
Claim 14
Dependent Claim
57 words
A is divalent phenylene or naphthylene; X is oxygen or sulfur; X' is oxygen or sulfur; Y and Y' are independently OR', N(R') 2 or SR', wherein R' is (C 1 -C 4 ) alkyl, (C 2 -C 4 ) alkoxyalkyl, (C 1 -C 4 ) haloalkyl, (C 3 -C 4 ) alkenyl, phenyl or substituted phenyl,
Claim 15
Dependent Claim
57 words
A is divalent phenylene or naphthylene; X is oxygen or sulfur; X' is oxygen or sulfur; Y and Y' are independently OR', N(R') 2 or SR', wherein R' is (C 1 -C 4 ) alkyl, (C 2 -C 4 ) alkoxyalkyl, (C 1 -C 4 ) haloalkyl, (C 3 -C 4 ) alkenyl, phenyl or substituted phenyl,
Claim 16
Dependent Claim
89 words
R 1 is hydrogen or a. (C 1 -C 4 ) alkyl; b. (C 1 -C 4 ) alkoxy; c. (C 3 -C 4 ) alkenyl; d. halogen; e. nitro; or f. a group of the formula: ##STR109## wherein t is carbonyl, sulfur, sulfinyl, or sulfonyl, provided that R 1 does not represent more than one ##STR110## group; and represents from one to four substituents when A is phenylene and from one to six substituents when A is naphthylene; and Z is a group of the formula: ##STR111## wherein
Claim 17
Dependent Claim
89 words
R 1 is hydrogen or a. (C 1 -C 4 ) alkyl; b. (C 1 -C 4 ) alkoxy; c. (C 3 -C 4 ) alkenyl; d. halogen; e. nitro; or f. a group of the formula: ##STR109## wherein t is carbonyl, sulfur, sulfinyl, or sulfonyl, provided that R 1 does not represent more than one ##STR110## group; and represents from one to four substituents when A is phenylene and from one to six substituents when A is naphthylene; and Z is a group of the formula: ##STR111## wherein
Claim 18
Dependent Claim
38 words
R 2 is a. (C 1 -C 4 ) alkyl; b. (C 1 -C 4 ) haloalkyl; c. optionally substituted aralkyl of up to 11 carbon atoms; or d. substituted or unsubstituted (C 6 -C 10 ) aryl;
Claim 19
Dependent Claim
38 words
R 2 is a. (C 1 -C 4 ) alkyl; b. (C 1 -C 4 ) haloalkyl; c. optionally substituted aralkyl of up to 11 carbon atoms; or d. substituted or unsubstituted (C 6 -C 10 ) aryl;
Claim 20
Dependent Claim
41 words
R 3 and R 4 are independently a. hydrogen; b. (C 1 -C 3 ) alkyl; c. (C 3 -C 4 ) alkenyl; d. (C 2 -C 4 ) alkoxyalkyl; or e. optionally substituted aralkyl of up to 10 carbon atoms;
Claim 21
Dependent Claim
41 words
R 3 and R 4 are independently a. hydrogen; b. (C 1 -C 3 ) alkyl; c. (C 3 -C 4 ) alkenyl; d. (C 2 -C 4 ) alkoxyalkyl; or e. optionally substituted aralkyl of up to 10 carbon atoms;
Claim 22
Dependent Claim
38 words
B is carbonyl, sulfinyl or sulfonyl; Q is alkylene of 2 to 4 carbon atoms; X" is oxygen or sulfur, provided that when X" is sulfur, X is oxygen; and n is an integer of 0 to 1.
Claim 23
Dependent Claim
38 words
B is carbonyl, sulfinyl or sulfonyl; Q is alkylene of 2 to 4 carbon atoms; X" is oxygen or sulfur, provided that when X" is sulfur, X is oxygen; and n is an integer of 0 to 1.
Claim 24
Dependent Claim
11 words
A compound according to claim 2, having the formula: ##STR112## wherein
Claim 25
Dependent Claim
10 words
A is ortho, meta, or para phenylene, or ortho naphthylene,
Claim 26
Dependent Claim
10 words
A is ortho, meta, or para phenylene, or ortho naphthylene,
Claim 27
Dependent Claim
69 words
Y is OR' and Y' is OR' or SR' wherein R' is a. (C 1 -C 4 ) alkyl, b. (C 2 -C 4 ) alkoxyalkyl; c. allyl; d. (C 1 -C 4 ) haloalkyl; e. phenyl; or f. phenyl substituted with (C 1 -C 4 ) alkyl, nitro, halogen, (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) haloalkyl, or di-(C 1 -C 4 ) alkylamino;
Claim 28
Dependent Claim
69 words
Y is OR' and Y' is OR' or SR' wherein R' is a. (C 1 -C 4 ) alkyl, b. (C 2 -C 4 ) alkoxyalkyl; c. allyl; d. (C 1 -C 4 ) haloalkyl; e. phenyl; or f. phenyl substituted with (C 1 -C 4 ) alkyl, nitro, halogen, (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) haloalkyl, or di-(C 1 -C 4 ) alkylamino;
Claim 29
Dependent Claim
59 words
R 1 is hydrogen or (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, halogen, benzoyl, benzenesulfonyl, benzenesulfinyl, or phenylthio; and represents from one to two substituents on the ring provided that R 1 does not represent more than one benzoyl, benzenesulfonyl, benzenesulfinyl or phenylthio substituent; and Z is a group of the formula: ##STR113## wherein
Claim 30
Dependent Claim
59 words
R 1 is hydrogen or (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, halogen, benzoyl, benzenesulfonyl, benzenesulfinyl, or phenylthio; and represents from one to two substituents on the ring provided that R 1 does not represent more than one benzoyl, benzenesulfonyl, benzenesulfinyl or phenylthio substituent; and Z is a group of the formula: ##STR113## wherein
Claim 31
Dependent Claim
78 words
R 2 is a. (C 1 -C 4 ) alkyl; b. (C 1 -C 4 ) haloalkyl; c. phenyl or napthyl, optionally substituted with from one to two substituents which are (C 1 -C 4 ) alkyl, nitro, halogen, (C 1 -C 4 ) haloalkyl, di-(C 1 -C 4 ) alkylamino, azidosulfonyl, (C 1 -C 4 ) alkylcarbonyl, (C 1 -C 4 ) alkylthio, (C 1 -C 4 ) alkylsulfinyl, (C 1 -C 4 ) alkylsulfonyl, or fluorosulfonyl;
Claim 32
Dependent Claim
78 words
R 2 is a. (C 1 -C 4 ) alkyl; b. (C 1 -C 4 ) haloalkyl; c. phenyl or napthyl, optionally substituted with from one to two substituents which are (C 1 -C 4 ) alkyl, nitro, halogen, (C 1 -C 4 ) haloalkyl, di-(C 1 -C 4 ) alkylamino, azidosulfonyl, (C 1 -C 4 ) alkylcarbonyl, (C 1 -C 4 ) alkylthio, (C 1 -C 4 ) alkylsulfinyl, (C 1 -C 4 ) alkylsulfonyl, or fluorosulfonyl;
Claim 33
Dependent Claim
70 words
R 3 and R 4 are independently hydrogen, (C 1 -C 4 ) alkyl, (C 3 -C 4 ) alkenyl, (C 2 -C 4 ) alkoxyalkyl, aralkyl of up to 10 carbon atoms, which is optionally substituted with up to two halogen atoms; provided that one of R 3 and R 4 is always hydrogen; B is carbonyl, sulfinyl, or sulfonyl; and n is an integer of 0 to 1.
Claim 34
Dependent Claim
70 words
R 3 and R 4 are independently hydrogen, (C 1 -C 4 ) alkyl, (C 3 -C 4 ) alkenyl, (C 2 -C 4 ) alkoxyalkyl, aralkyl of up to 10 carbon atoms, which is optionally substituted with up to two halogen atoms; provided that one of R 3 and R 4 is always hydrogen; B is carbonyl, sulfinyl, or sulfonyl; and n is an integer of 0 to 1.
Claim 35
Dependent Claim
53 words
A compound according to claim 3 wherein R' is (C 1 -C 4 ) alkyl, (C 2 -C 4 ) alkoxyalkyl, allyl or (C 1 -C 4 ) haloalkyl, B is carbonyl or sulfonyl, and R 1 is (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, halogen or benzoyl.
Claim 36
Dependent Claim
6 words
A compound having the formula: ##STR114##
Claim 37
Dependent Claim
6 words
A compound having the formula: ##STR114##
Claim 38
Dependent Claim
6 words
A compound having the formula: ##STR115##
Claim 39
Dependent Claim
6 words
A compound having the formula: ##STR115##
Claim 40
Dependent Claim
6 words
A compound having the formula: ##STR116##
Claim 41
Dependent Claim
6 words
A compound having the formula: ##STR116##
Claim 42
Dependent Claim
22 words
An anthelmintic composition for oral administration comprising an anthelmintically effective amount of the compound of claim 1 and a pharmaceutically acceptable carrier.
Claim 43
Dependent Claim
22 words
An anthelmintic composition for oral administration comprising an anthelmintically effective amount of the compound of claim 2 and a pharmaceutically acceptable carrier.
Claim 44
Dependent Claim
22 words
An anthelmintic composition for oral administration comprising an anthelmintically effective amount of the compound of claim 3 and a pharmaceutically acceptable carrier.
Claim 45
Dependent Claim
22 words
An anthelmintic composition for oral administration comprising an anthelmintically effective amount of the compound of claim 4 and a pharmaceutically acceptable carrier.
Claim 46
Dependent Claim
22 words
An anthelmintic composition for oral administration comprising an anthelmintically effective amount of the compound of claim 5 and a pharmaceuticaally acceptable carrier.
Claim 47
Dependent Claim
11 words
A composition of claim 8 in the form of a tablet.
Claim 48
Dependent Claim
13 words
A composition of claim 8 in the form of a flavored, chewable tablet.
Claim 49
Dependent Claim
12 words
A composition of claim 8 in the form of a flavored liquid.
Claim 50
Dependent Claim
27 words
A method for combatting a helminth infection in a host animal which comprises administering an anthelmintically effective amount of a compound of claim 1 to said animal.
Claim 51
Dependent Claim
12 words
The method of claim 16, wherein the host animal is an avian.
Claim 52
Dependent Claim
12 words
The method of claim 16, wherein the host animal is a cat.
Claim 53
Dependent Claim
12 words
The method of claim 16, wherein the host animal is a dog.
Claim 54
Dependent Claim
12 words
The method of claim 16, wherein the host animal is a sheep.
Claim 55
Dependent Claim
12 words
The method of claim 16, wherein the host animal is a porcine.
Claim 56
Dependent Claim
12 words
The method of claim 16, wherein the host animal is a bovine.
Claim 57
Dependent Claim
12 words
The method of claim 16, wherein the host animal is an equine.
Claim 58
Dependent Claim
11 words
The method of claim 16, wherein the host animal is man.
Claim 59
Dependent Claim
26 words
The method of claim 16, wherein the compound is administered at a dosage of between about 3 and 500 mg/kg of body weight of the host.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-02-27 | 1981-08-29 | 1982-02-28 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-02-27 | 1985-08-29 | 1986-02-28 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-02-27 | 1989-08-29 | 1990-02-28 | $7700.00 | Window Closed / Lapsed |